Dog Friendly Hiking Trails in Old Chatham, NY

Leashed dogs are welcome to join you as you explore the pet-friendly grounds of the Norman Rockwell Museum in Stockbridge, MA. The museum houses the world’s largest and most significant collection of Rockwell’s work. While Fido can not browse the artwork inside, the grounds offer 36 acres to explore, including sculptures, lovely landscaping, scenic views and picnic tables. Note that pets may not be left unattended in cars or anywhere else for owners to enter the museum.

Walk your leashed dog at Scenic Hudson's Long View Park in Coxsackie, NY. The first thing that greets you upon entering the park is an old red barn, which attests to the land’s centuries-long history as a farm. The park is open daily from dawn to dusk.

Leashed dogs are allowed at Monument Mountain Reservation in Great Barrington, MA. This pet-friendly natural space features beautiful and moderately strenuous hiking trails. One trail reaches the 1,642-foot summit of the mountain and offers incredible Housatonic River Valley views.

Olana State Historic Site is a historic house museum and property in Greenport, New York, near the city of Hudson. The estate was home to Frederic Edwin Church, one of the major figures in the Hudson River School of landscape painting. Access to Olana’s dog-friendly, 250-acre landscape is free. The park is open every day from 8 AM to sunset. Bring Fido to explore Frederic Church’s designed landscape with five miles of carriage roads as a way to enjoy the outdoors.

Leashed dogs are welcome at Pittsfield State Forest, a pet-friendly natural area in Pittsfield, MA.There are 30 miles of trails to explore at this huge, 11,000-acre park, including the Taconic Crest Trail and the Tranquility. Berry Pond is also a popular spot in the park that offers swimming and fishing opportunities.

High Falls Conservation Area is a pet-friendly natural preserve in Hudson, NY. This natural wonder boasts beautiful waterfalls that are surrounded by trees. Four-legged friends are welcome to join you for a walk on one mile of winding trails. Dogs must be leashed and cleaned up after.

Olivia’s Overlook, located in West Stockbridge, MA, offers a beautiful vista view and access to several dog-friendly hiking trails within the Yokun Ridge South reserve. Leashed pups are welcome to join you on your outdoor adventure through forests, ridgelines and peaceful paths. It's a scenic spot perfect for a relaxing walk or a longer hike with your four-legged friend.

Erie Canalway Trail is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Albany! The map below shows a parking area with convenient access to the Erie Canalway Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com.

Greenport Conservation Area is a pet-friendly recreational space in Hudson, NY. This over 600-acre natural preserve consists of trails and open fields with views overlooking the Hudson River. Fido is welcome to join you on a hike as long as he is leashed and cleaned up after.

Parsons Marsh Trail in Lenox, MA, offers a scenic dog-friendly walk through the woods. This 0.6-mile round-trip trail features a mix of packed trail and elevated boardwalk, making it accessible and easy to navigate. Built in 2018 to U.S. Forest Service accessibility standards, it’s a great spot for a peaceful stroll, geocaching or a picnic with your pup.

Leashed dogs are allowed at Beartown State Forest in Monterey, MA. Home to a 12,000-acre forest and Benedict Pond, you and Fido can take on the pet-friendly Benedict Pond Loop Trail, which circles the scenic pond. Although a nice location year round, one of the best times to visit is in autumn to enjoy the breathtaking fall foliage.

Leashed dogs are welcome at Cherry Plain State Park, a pet-friendly recreation area in Petersburgh, NY. You and Fido can enjoy hiking, biking and cross-country skiing the park's trails. Boating, fishing and camping are also popular. You can bring a maximum of two pets and they must remain on a six-foot or shorter leash throughout your entire visit. Proof of a current rabies vaccination must be present. Pets aren't permitted in playgrounds, buildings, golf courses, boardwalks, pools and spray-grounds, or guarded beaches. Please clean up after Fido.

Coxsackie Riverside Park is a pet-friendly spot in New York. Wander with your pup along the trails of this popular park and enjoy the colors of fall on the trees around you. Home to a yearly blessing of the animals, this is a great place to visit with your dog and see somewhere new.

Erie Canalway Trail is one of 1600 rail-trails supported by Rails-to-Trails Conservancy, a nonprofit organization that is working to create a nationwide network of trails from former rail lines and connecting corridors. Previously an unused railroad corridor, this "rail-trail" is now a great place to walk Fido in Watervliet! The map below shows a trailhead where you can pick up the Erie Canalway Trail. Rails-to-Trails Conservancy has generously provided map data for this trail to Bring Fido for informational purposes only. For more detailed trail information, please visit TrailLink.com.

East Mountain State Forest is a pet-friendly route in Great Barrington, MA. Your leashed canine companion can tag along as you hop on this challenging trip along the Appalachian Trail. The area features four beautiful overlooks with views of three states. Please note the terrain is rugged and that the area is a habitat for coyotes, bears, deer, and turkeys.